Abstract
Levoglucosenone reacts with α-aminoazoles to yield azolo[1,5-a]pyrimidine systems fused with a carbohydrate fragment. The reaction oocurs much more smoothly than in the case of other α,β-unsaturated ketones. The reactions of levoglucosenone with β-dicarbonyl compounds (dimedone, barbituric acid) in the presence of a base results in the pyran ring closure, which has never been observed earlier in reactions of β-dicarbonyl compounds with α,β-unsaturated ketones under the conditions of basic catalysis. The structures of products were established by IR and NMR spectroscopy.
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For Part 3, see Ref. 1.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 553–558, March, 1997.
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Samet, A.V., Yamskov, A.N., Ugrak, B.I. et al. Synthesis of heterocyclic systems with a carbohydrate fragment. Russ Chem Bull 46, 532–538 (1997). https://doi.org/10.1007/BF02495410
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DOI: https://doi.org/10.1007/BF02495410